Crank or Champion?

Editor’s note: A shorter version of this story appeared in the April 15 print edition of The Observer.

“Prince Street belongs to me. I’m sorry—it’s turf.”

Sean Sweeney, president of the Soho Alliance, was talking in late March about bike lanes. He could’ve been talking about political races. Restaurants. Condo-hotels. The thing doesn’t matter so much as the location: the blocks just below Houston. “I don’t go above 14th Street,” he said in late March. “I get hives.”

From his Greene Street loft—bought for around $100,000 in the early 1980s—Mr. Sweeney, 63, directs a potent NIMBY machine that has engendered equal parts fear, loathing and love in the downtown diaspora. There, he hosts meetings of the Downtown Independent Democrats, where he’s been president since 1997 (with one four-year hiatus). He chairs Community Board 2’s Landmarks Committee. And the loft has unofficially headquartered the Soho Alliance since the group installed its phone and answering machine in a corner, sometime during the tail end of the Dinkins administration.

Mr. Sweeney is home about 90 percent of the time to answer it. He speaks quickly, with a force that overmatches his stature, even carrying himself ramrod-straight. Never married—“I don’t like institutions,” he explained—he still eats porridge and lives with his elderly mother, whom he cares for affectionately. It’s fitting: Territoriality is a family tradition.

Born in an Irish Republican ghetto of Glasgow, his parents gave him the good British name of John for his own protection, but wrote the name he would later take—Sean—on the back of a now yellowing birth certificate, which he produced from a leather briefcase. When Mr. Sweeney was 3, his family moved to Brooklyn, where he grew up waging campaigns against Catholic school authorities.

He landed in Soho in the 1970s, where by night he managed the Loft, an invite-only house party where drugs flowed like water. By day, he picketed the British Consulate, and worked with Irish Northern Aid to send money back home.

“The bosses were bad, and the landlords were bad,” he says of his upbringing, steeped in Labor politics. He doesn’t much care for developers, either, nor they for him. Mr. Sweeney wakes up every morning to the sight of the Trump Soho condo-hotel, which he claims to have pushed into near foreclosure. The completed tower is slated to open this fall, according to reports. (A representative for the developers declined to comment for this story.)

In his mid-40s, Mr. Sweeney put his money in the stock market, and hasn’t worked since. Now, he lives off that, plus a rental property in Montauk and the sale of his mother’s old home in Glasgow. His full-time activism is all-volunteer; he finances the Soho Alliance’s lawsuits—which average about $20,000 each—largely through donations raised from co-op boards. Until recently, the litigation was also underwritten by S&M club proprietor Don MacPherson, who last month was arrested for mortgage fraud in the Hamptons (Mr. Sweeney thinks he’s innocent).

“Hey, do you want to sleep?” he said, describing the club’s MO. “Have someone come to a Soho Alliance meeting, and contribute $1,000, and you sleep.”

Mr. Sweeney has never aspired to higher political office himself—he never bothered to become an American citizen. No matter: In private, politicians have started to call him Boss Sweeney, as a compliment.

NEARLY THREE DECADES OF BEING a professional pain in the ass have born significant fruit. “He has created a political structure in Soho that candidates, city agencies and elected officials ignore at their own peril,” according to the current Community Board 2 chairman, Brad Hoylman, who says Mr. Sweeney’s opposition had a lot do with his failed City Council race against Alan Gerson in 2001.

“He’s a force of nature,” agreed freshman State Senator Daniel Squadron, who got a toehold in Soho when the Downtown Independent Democrats endorsed him over incumbent Marty Connor. “I knew, if I’m going to run for this seat, I’m going to need to know Sean Sweeney.”

Soho residents usually hear about the latest outrage through his strongly worded flyers about hearings and races. The ones for the Downtown Democrats are called “D-Notes,” colored pamphlets that bear Mr. Sweeney’s name along with the politicians he’s endorsing. “When this goes out with my name on it,” he said, flicking the green pamphlet, “They go, ‘Oh, yeah, I don’t know who this guy is, but I know Sean, he’s a nice guy.’”

Over 30 years, however, enemies mount as quickly as friends.

Mr. Sweeney has railed against a Department of Transportation that dares put down bike lanes without asking him first. Having fought the imposition of the Lower Manhattan Expressway in the 1960s, he calls the progressive DOT commissioner, Jeanette Sadik-Khan, “Robert Moses in a skirt.”

“We defeated Moses, and we’re going to defeat Sadik-Khan. I’ll be around and she’ll be gone. Got it? Quote,” he said. “She’s not been nice to me. …”

“I think that old radicalism really resonates with many of his constituents in SoHo,” mused Paul White, head of Transportation Alternatives, which has butted heads with the Alliance over bike lanes as well. “People rally around fighting the imperialist City Hall without paying attention to the details of what are offered.”

After helping him to victory eight years ago, Mr. Sweeney is now feuding with Councilman Alan Gerson, saying he’ll back “anyone but Gerson” for that seat and heckles the councilman at city events. “Basically, he lied to me too many times, has no sense of gratitude, has ignored Soho,” Mr. Sweeney said.

And then, of course, there’s the four-year battle over Lola, the partly African-American–owned soul-food restaurant on Watts Street that the Soho Alliance litigated into bankruptcy earlier this year. That, combined with Mr. Sweeney’s decision to hold a community board committee meeting on Martin Luther King Day, has led to allegations of racism from many sides.

“Little bit of a bigot there,” said longtime downtown operative Ray Cline, a consultant at Progressive Strategies Group. “He doesn’t get along with black folks.”

Though Mr. Sweeney brushes off the charge, it clearly still rankles. He pulled from his briefcase a crinkled photo of himself with the staff at the Loft, mostly black: “I did more to integrate Soho than Lola ever did.”

LATELY, HE’S EVEN MADE ENEMIES within his own political club. In April of last year, Mr. Sweeney faced a challenge from relative newcomer Pat Moore, after years of uncontested elections. He calls it a coup engineered by the Community Board 1 chairwoman, Julie Menin, who wanted the Downtown Independent Democrats’ backing for a prospective City Council campaign. Allegations of vote-stacking flew on both sides. Ultimately, he called off the election on a technicality.

Former ally David Reck, a community board member and president of Friends of Hudson Square, says Mr. Sweeney turned against him over a vote on a bike lane two years ago (Mr. Sweeney claims the fight got physical, which Mr. Reck denies). Now, Mr. Reck is working to oust him as head of the Downtown Democrats, or even start a new club.

“Sean has become the petty little dictator of it all,” said Mr. Reck, meaning the Soho Alliance as well. “Something’s got to be done, because Sean has become a tremendous problem.”

“There is so much potential in the club, and it’s not used at all,” sighed Ian Dutton, who ran and lost against Mr. Sweeney last year after serving two years as vice president. “I just feel like he gets up in the morning and decides who he’s going to make miserable.”

Mr. Sweeney has his defenders, like club founder and bar owner Jim Stratton, who—like his successor—cherishes old Soho. “The problem that Sean has is shooting from the hip a little bit,” Mr. Stratton says. “He’s got a good Irish temper. But then he calms down.”

For his part, Mr. Sweeney says that having won an actual contested election has only raised his profile in the party apparatus. But he admits to having had a hard time sleeping after the aborted elections last year.

“I don’t like rejection,” he said. “I have a weakness for that. I want people to like me.”

For those who attack him, Mr. Sweeney has a favorite saying: “Let no good deed go unpunished.”

“That’s what a lot of humanity is like. What have you done for me recently, Sean?”